The Miltons vs Winchesters
by StarlovedHeroine
Summary: This is my high school story. The Milton's are the upper class and Winchesters are beneath them sometimes in more that one way. Rated M- there will be sexual content even in chapters where characters might not be of age. Language of curse and some violence. Dean/Cas Sam/ Gabriel are the main pairings but might add others dunno yet.


**Ok I thought I would do a high school one too, I will be writing more for my other one soon for those who are reading it. but this one just right into the smut lol.**

**WARNING RATED M-Sex, language, eventually violence and etc.**

* * *

The Milton's were Lawrence's answer to the Kennedy's. Rich, powerful, beautiful and always news worthy, but seemed tragically cursed. Their grandfather died in a train accident, their grandmother was burned alive, their mother died giving birth to the youngest of them and their father seemed to be MIA. No one had seen Mr. Milton in years he was presumed dead by most of the town and the kids at school. But the children seem to be reaping the benefits of their family's tragic past. Five of them still lived in the estate named, Heaven's Haven, on the outskirts of town.

There was Michael, Raphael, Gabriel, Anna, and Castiel, the baby of the group. Their brother Nick was in prison from attempted murder, trying to kill his brother Raphael. The others don't know why he did it but he was always a black sheep of the family. Michael was the head of the house when he wasn't away on business, keeping up the Milton's fortunes. Raphael seemed to be his lackey always at his brothers bidding, which left the younger three alone a lot, well sort of they had their security headed by an imposing man named Uriel, their cook Ellen and her daughter who was pretty much the female playmate of Anna's as she grew up. But now that high school had hit Anna and Jo barely talked. But Jo was still the only outsider from school allowed in their house without an invitation.

Gabriel graduated the year before and was taking a sabbatical before attending some form of higher education. Anna was a senior and pretty much queen b at the school, because she was nice and beautiful, but could have a malicious side if pushed. Castiel was a junior but could have graduated already but he didn't like the thought of making his family feel inferior to his mind but didn't mind flaunting it at school. Anna had her friends in the highly manipulative Meg and the only other girl who would come over to their house when they were little, a girl named Ruby, Ruby's big sis Lilith always had a thing for Gabriel and hated the fact he rejected her. Castiel's friends where his family and a British boy named Balthazar and Lilith seemed protective over him as well.

The Milton kids were known for having wild parties filled with sex, drugs, alcohol, and sometimes the occasional fight. But you couldn't come to the parties unless you were invited and the list was exclusive. Someone who never got invited was Dean Winchester and his brother Sam for that matter. In fact most of Dean and his friends never received an invite. They were from the other side of the tracks. Their dad was a mechanic and granted they owned their house but any extra money they earned was put into keeping the house in one piece. Its Dean's senior year and he had never had a soft spot for the Milton's thought they were bitches and douche bags like some magicians.

Anna never invited Dean to the Milton parties because of Meg and the fact he turned her down every time Meg would even think of slumming with the mechanic's son. Anna would never admit but if Meg was going to try to slum she did pick a bit of eye candy. Anna had to take her car to Dean's dad's shop one hot day over the summer and Dean was standing outside with his mechanics jumper unzipped and tied around his waist, a grease covered white wife beater on and a bit of dirt smudged down his sweat glistening arms. She watched as he slowly took a drink his lips perfectly fitting around the bottle top, his freckles hidden behind some dirt. He did have a certain charm, but she would never admit it.

Now it was the last week in October and school was going as normal. The Milton's and there crew acting like the owned the school and Dean's group not falling at their feet begging for an invitation to their Halloween party. Possibly the most hyped party the Milton's ever had.

Dean laid with his back flat on the bleachers as the Milton's used the football field to hand out the invite. Sam sat a level lower going through his books and scribbling notes down as he tried not to look to see who was actually getting invites. Jo sits down using Dean's legs as her seat and he pushes himself up and Ash sits down next to Sam, straddling the bleachers. Jess joins the group smiling softly at Ash and slowly taking Sam's arm. Dean looks over at the show.

"It's my last year here…I just feel like it wouldn't be complete unless I crashed a Milton party," He smirks Dean wasn't really known for being the most well behaved boy and trouble just seem to be his main vice.

"I don't think that's such a good idea Dean," Sam said looking up at him as the group looks at him.

"When have I ever had a good idea…I think it's a great one…and fun. I would love to toss a little chaos into their perfect little world," Dean smirks," Besides if we could we could bring them down a couple notches."

"You sound jealous Deano," Jo stated pushing her blonde hair off her shoulder but looks over at him with a smirk. "But if you really want too I can get you in."

"Jo you are not helping here," Sam stated as Dean's mischievous smile grew wider.

"We're going Sammy…Ash do your thing round us up some costumes," Dean pats Ash on the shoulder and Ash nods accepting the order.

"I'll be fun Sam…I can see if Brady want to come…" Jess encouraged.

"Now I'll go but don't mention it to Brady…we're not talking," Sam side glanced at Jess a bit and she blushed under his stare.

"Ok then its settled we'll meet at my house on Friday around five to get ready," Dean smirked as he began formulating ideas so shit he can do to cause issues at the party.

** -\m/\m/- **

Halloween rolled around quickly but Dean managed to get some flash bombs and fireworks from his Uncle Bobby's house. He knew Bobby would be for causing a ruckus at the Milton's after all it was Nick who killed Bobby's wife. Dean pull all his other supplies in a bag with moved with a squeak in the outfit Ash had gotten for him. Dean sneers as he looks in the mirror and checks himself out pursing his lips together under the black mask and adjust his cock in the tight outfit. He comes down out of his room.

"Dude Ash could this outfit had gotten any tighter…and dude Ash what the hell are you supposed to be," Dean motions to Ash who looks like he always does, mullet and all.

"I'm old school Billy Ray Cyrus. Hot right?" He grins and flex his arms and Dean just shakes his head slowly. Ash flicks his mullet off his shoulder and seriously thinks he looks irrespirable.

"They're going to recognize you dude," Dean says. "Nope," Ash pulls out a pair of dark sun glasses, "I'm totally incognito."

"Yeah, Ash totally," Jo says with sarcasm dripping from her voice but it doesn't seem to effect Ash. Dean eyes her over and smirks. She is wearing a slutty little red riding hood costume that Ash had brought for her. She plays with the cape as she looks Dean over in his batman costume. "My my my if it isn't the next Val Kilmar…you do know they remade that series right."

"Jo shut up…"Dean looks down at the black vinyl costume.

"It's the lips Deano," She walks over and squeezes his cheeks making him purse his lips out more. Dean rolls his eyes and lightly knocks her hand away.

"Where's Sammy…? And Jess," Dean had hoped Jess would have backed out on the party crash but it was Jess who inspired Sam to come so he wouldn't bitch if she tagged along.

Moments later Sam walks down dressed in a loose fitting pair of scrubs with the white mask and cap. Jess was dressed as his slutty nurse. Dean glares at them and then turns to Ash.

"What the hell dude…why do I get stuck in the geek costume?" Dean glares at him threw the mask.

"They wanted to match…" Ash looks around like he didn't seem what the problem was as Dean throws his hands up in an exasperated breathe.

"Let's just go!" Dean leads the group out to the Impala before heading across town to the Milton's.

** -\m/\m/- **

Dean parks the Impala down the road from the party and the group snuck around and threw the garden gate which Jo had a key for. They all smiled seeming to have achieved something as they made their way into the party from the kitchen area.

"Just act like you belong and they'll be less likely to notice you, if you get offered a drink take it, and Sam don't look like a worried grouch it's a dead giveaway," Jo pointed to his face as Dean chuckles. Sam rolls his eyes and applies a smile to his face and Jess giggles. "Better." Jo noted before they turned the corner and walked into the party.

Jo and Ash head over to the drinks as Jess looks at Sam then points to the snacks and Sam moves over next to Dean. "I don't think this is such a good idea."

"Dude Sammy live a little…I'm going to check up stairs to see where I can set theses up," Dean taps the bag. Sam shakes his head and turns to say more to Dean but Batman is already up the steps.

Sam rocks in place a bit and looks around the party. He straightened his shoulders so he wouldn't seem so uncomfortable. He managed to pin point Anna and her gaggle of she witches before he walked further into the party so he knew where to avoid going_. Where is Jess, is she like eating all the snacks?_ Sam thought as he looked back over to the snack bar and narrowed his eyes as he saw Brady talking to Jess. He swears under his breathe.

"Domestic troubles Doc?" Sam tried not to appear as startled as he was by the playful voice that seemed to emerge from nowhere. Sam turns and sees Gabriel standing there holding two bottles of beer. He pushes his arm up against Sam's trying to coax his to take the beer but Sam was lost in his honey eyes. "Milton house rule, no one goes without a drink Doc."

Sam looked down at the beer and slowly took it wrapping his figures around the cold neck of the beer with intensified the chills he received from caressing Gabriel' fingers slightly. Sam had known for a while that it was right to label people an if you found someone attractive you found them attractive and there was just something he had always found alluring about Gabriel Milton. I smiled under his scrub mask as he took the beer.

"I…thanks. I was heading that way," Sam lied and Gabriel laughed his eyes gleaming.

"No need to lie, lying is a sin you know and it never benefits anyone…I'm Gabriel," Gabriel extends his hand.

Sam gasps lowly but slowly takes his hand and shakes it. Gabriel looks up at him with a smirk clear expecting a name. Sam slowly cleared his throat and in a low voice, "Let's just call me Doc tonight."

"Interesting," Gabriel said slowly as he circled Sam, "So Doc…accepting any new patients I think I need a full body examine."

Sam's voice seemed to get stuck in his throat and Gabriel ran the back of his fingers up Sam's arm slowly getting pleasure from the look in Sam's eyes. Jess finally came over to Sam and Gabriel dropped his hand quickly and Jess took Sam's arm. Sam seemed a little disappoint as Jess softly excused them and dragged him away.

Meanwhile Dean was upstairs looking and trying to find an unlocked door.

"I would say if you're looking for a little fun with Robin you're in the wrong part of the house only you riding solo tonight eh Batman?" Dean stops in his tracks. Busted! Fuck. He thought as he turned to be greeted by a scantily clad French maid with a heaving bosom and long blonde hair. It took all of Dean's power to look away from her chest and she noticed smirking," This part of the house is off limits."

"Then what are you doing here?" Dean said in a very low scruffy voice.

"Me…I'm allowed, that's what being me gets you." She smirks moving closer to Dean.

"And who would you be?" Dean knew damn well who he was but he was playing dumb, something he was very good at.

"Lilith…the maid," She runs he hands over her body and smirks as Dean follows them. "Just be glad it was me that found you up here and not Uriel. He would have removed some…" Lilith trails a hand down the costume and over his cock as Dean forces down a dry gulp."…very precious parts. But I found you so we're going to have a little fun." Lilith winks at Dean as she pulls him down the hall and into a room that he hadn't checked yet.

Dean looked around the darkness of the room. The only light as the moonlight coming in from the window, the only sound was the distant sound of the music from the party. Dean started to get worried as Lilith pulled his bag off his shoulder and placed it on the floor. Dean sees a shadowy form push up from a bed and Lilith squeezed his bicep.

"I know you should you were done with the party for tonight but you can let Brady get too you, and since I can't stand to see you this way I brought you a treat…" Lilith teased to the shadow.

"Look lady I am no one's treat, you make me sound like a chew toy or something," Dean turned towards her voice.

"Oh please my Sassy lil one only bites his you beg," Lilith noted and a light laugh can be heard from the bed. "No Batty be a good boy, if I get a bad review I will hurt you worse than Uriel ever would have…Now play nice you two."

Lilith moved from Dean's side and goes back out the door. Dean felt lost and didn't know what to expect as a light cut on. Dean was a little surprised to see the short tousled black hair and bright blue eyes of the youngest Milton staring him down. Castiel stood up and Dean felt his stomach flutter as he stared at the boy's chest as his costume left his chest open for all to view and the harem pants he wore hit right at the pelvic hip bone grove. Dean bits on his lower lip he had never thought Aladdin was good look, Jasmine yeah he would bang her, but Aladdin never looked good till Castiel was in the outfit.

Dean had never thought about the youngest Milton much he knew Anna was hot but a bitch and Gabriel he found annoying, and don't get him started on the older three. Castiel just never hit Dean's radar till now. Dean watched him move closer to him and stop directly in front of him. Castiel tilted his head slightly and Dean's eyes feel to his full lips. Dean had never known a man to be this attractive before.

"Who are you?" Castiel spoke in a deep gravelly voice that nearly made Dean weak in the knees due to the silence that had been between them.

"Bruce Wayne." Dean got out sarcastically.

"Funny," Castiel said slowly still not laughing. "I'm Castiel."

"What are you going to do with me, Castiel?" Dean almost hesitated to ask the question.

"Nothing you won't enjoy in the long run," Castiel said with a smirk and before Dean could speak Castiel's lips were on his. It felt weird being kissed with the mask on but Dean was thankful for it when he began to kiss back bring a hand up and wrapping it in Castiel's hair. Dean felt him moan slightly against his lips as he pulled lightly on his hair.

Dean's cock twitched interested in what else Castiel could do with that mouth. Castiel breaks the kiss and runs his tongue seductively over Dean's lips before sucking on his lower lip. Dean never even knew Castiel went this way but then again he didn't know much about him. Castiel goes to lift the mask up and Dean catches his wrists with both his hands.

"You can do whatever you want but the mask stays on." Dean slowly lowers his hands.

Castiel smirks as Dean releases his hands, and as if knowing how to work the batman costume better than Dean did getting it on gets Deans cock out. Dean gasps and groans at the speed in which he did it. Castiel smirks and bites his lower lip and pulls his cell phone off his dresser near the door.

"What are you going to do with that?" Dead questions and Castiel grins.

"Well since I don't know you I'm going to take a picture of your cock…It's a beautiful thing," Castiel states in his husky voice as he raised the camera up with one hand and slowly reaches down and runs one finger softly along the length of the underside of Dean's cock. Dean growls deep in his throat as Castiel slowly caresses his dick and then slowly moves his hand down to Dean's balls massaging them as he puts the camera down and presses against Dean. "I think the picture would look even better if you were completely erect. Don't you think?"

Castiel pecks at Dean's lips as he slowly drops to his knees extending his tongue out and licking the tip of Dean's cock teasingly. "Besides you said I could do whatever I wanted as long as your mask was on." Castiel reminded Dean before it ran his tongue around Dean's head pressing it firmly against his tip and licks the precum off of it. Castiel takes his hand and lifts Dean's dick up and runs his tongue firmly up the underside letting it drop freely into a full erect position. He smirks and pulls his phone back up and leans back a bit. Dean closes his eyes as the flash goes off.

"Wunderbar, hmmm… want to see?" Castiel gets off his knees and slides up Dean's body. Dean can feel Castiel's own straining hard on threw the fabric of the harem pants against his cock as Castiel presses close to him and shows him the picture on his phone. Dean felt his cheeks blaze red once again thankful for having the mask still on. Castiel's blue eyes deepened to an oceanic color and Dean could almost feel himself drowning in them. Castiel presses his lips to Dean's once more slowly at first as Dean grabbed his neck again and pushed him backwards and they both eventually fell upon Castiel's bed.

"Getting excited Batman?" Castiel says in a low growl right next to the hole for Dean's ear after he broke the kiss.

"You could say that…" Dean finally choked out after coming back to his senses as much as he could given his painfully hard erection pressing against Castiel's clothed erection.

"Good, now promise no tricks tonight and I'll give you a treat," Castiel sat up pressing his hips down against Dean. Dean groans as he notices Castiel glancing over at his bag. Dean really wanted to ruin this party but Castiel has him so hard he couldn't even function so he decided to give into the little blue eyed devil.

"Promise…no tricks as long as you give me a treat…and I don't mean candy," Dean leans up and hooks an arm around Castiel's back and brings him in kissing him hard nearly bruising Castiel with the mask but Castiel quickly adverted the mask to reach Dean's full lips. Castiel broke the kiss and slowly pushed Dean back.

"I really wish I could get a name Batman, but I guess I'll just have to settle for making to moan mine," Castiel said in his seductively gravelly voice, Dean couldn't help but groan.

Castiel slides down Dean's body till his knees hit the floor. Castiel parts Dean's legs and slowly moves up to his aching member. Dean sits up on his elbows and watches Castiel teasingly blow against his cock the cool air making it twitch. Dean's eyes all but roll out of his head as he felt Castiel's warm mouth envelope his cock. The warmth and wetness made Dean's pulse quicken as he felt Castiel's hand come up and work his balls. The boy knew what he was doing and Dean couldn't help but wonder how much experience he actually had at it.

Dean slowly slid a hand into Castiel's soft hair, wrapping his fingers around the dark tresses as he tilted his head back with a moan. Castiel loosened his throat and took Dean in until his head was meeting the back of his throat and he repeated the motion over and over again till Dean lost his grip on his hair and hand to use both his elbows too keep him up so he could watch Castiel work. The damn costume hindering Dean's movements. He was really wishing he was naked right now.

"Fuck…Cas…uhhh," Dean licks his lips as Castiel pulls his cock all but out of his mouth, using the head like a lollipop and jerking his shaft with his hand. Castiel laughed a bit at the nickname sending a shiver through Dean. Dean knew he couldn't hold his climax back but longer but he fought it wanting to see what else Castiel could do. Dean loved the feel of being in his mouth and his slender fingers wrapped around his cock. Dean had never wanted to climax so soon before, no girl has ever worked him this way.

"You're going to come soon aren't you," Castiel said as he pulled his mouth off Dean as Dean whimpered at the abrupt stop. Castiel slowed his jerking down eventually letting his hand rest gripping he base of his cock. "I want a hint."

"A hint about what?" Dean almost snapped at him not liking the teasing that was going on.

"About who you are Batty…So give me a hint or…" Castiel shakes Dean's cock in his hand a bit," You'll have to leave the party like this."

"Are you serious dude?" Dean clenched his fist against the sheets.

"Afraid so…so what's it going to be?" Castiel leans down and licks up on side of Dean's shaft and over the top and down the other side slowly.

Dean feels his hips wanting to lift up and his eyes roll back again. He finally locked his own lust blown eyes with Castiel's, "What do you want to know?"

"What school do you attend and grade?" Castiel smirks at Dean and lowers his head back down over his cock waiting to hear the answer before he would continue.

Dean didn't want to answer cause that would almost give him away, Castiel was clever in his way of getting information out of Dean, cause Dean knew despite not wanting to reveal who he was he was going to answer the question. Cas was just too good at what he did for Dean not to want him to finish. Dean lets out a sigh," Senior and Lawrence High."

"Oh… so I might know the Bat," Castiel grins and takes Dean back into his mouth_._

_Fuck fuck fuck he is going to try and figure me out…maybe he won't maybe it was just a teasing ploy, he is a Milton after all they love to make people's lives hell_. Dean thought before he could no longer think giving himself over the pleasure Castiel was causing him Dean's hips buck up as he puts a hand back in those black locks holding Castiel in place while he came. Castiel swallowed his down licking him clean as he removed his head. Castiel crawled back up him and let their eyes meet seemingly studying Dean's eyes. Dean couldn't help but fall under the spell of those gorgeous blue eyes.

"See you at school then," Castiel said lowly with a smirk in his voice as he got up off Dean and moved over to his personal bathroom." You can see yourself out."

Castiel disappeared into the little room and Dean laid there for a minute processing. He quickly gathered himself and managed to get his cock back into the costume threw the hole Castiel had pulled it out of. He stands himself up and slowly walks over grabbing his bag and glances back at the bathroom door before exiting.


End file.
